Tris[4-(methyl-sulfan-yl)phen-yl]arsine.

In the title compound, C(21)H(21)AsS(3), the three benzene rings make dihedral angles of 88.41 (10), 87.75 (9) and 74.74 (10)° with each other. The methyl-sulfanyl groups are roughly coplanar with their attached benzene rings [C-S-C-C torsion angles = -7.6 (2), 11.2 (2) and 4.1 (2)°]. In the crystal, weak C-H⋯π inter-actions link the mol-ecules.

Related literature

For related structures of tris­aryl­arsines with osmium and ruthenium, see: Cullen et al. (1995 ▶); Shawkataly et al. (2009a ▶,b ▶, 2010a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H21AsS3

M = 444.48

Monoclinic,

a = 11.0839 (2) Å

b = 11.4556 (2) Å

c = 17.3247 (2) Å

β = 110.860 (1)°

V = 2055.58 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.96 mm−1

T = 100 K

0.35 × 0.13 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.545, T max = 0.821

31130 measured reflections

7111 independent reflections

5098 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.097

S = 1.01

7111 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002876X/hb5559sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002876X/hb5559Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H21AsS3	F(000) = 912
Mr = 444.48	Dx = 1.436 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6720 reflections
a = 11.0839 (2) Å	θ = 2.7–31.0°
b = 11.4556 (2) Å	µ = 1.96 mm−1
c = 17.3247 (2) Å	T = 100 K
β = 110.860 (1)°	Block, colourless
V = 2055.58 (6) Å3	0.35 × 0.13 × 0.11 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	7111 independent reflections
Radiation source: fine-focus sealed tube	5098 reflections with I > 2σ(I)
graphite	Rint = 0.051
φ and ω scans	θmax = 32.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
Tmin = 0.545, Tmax = 0.821	k = −11→17
31130 measured reflections	l = −25→25

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0486P)2] where P = (Fo2 + 2Fc2)/3
7111 reflections	(Δ/σ)max = 0.001
229 parameters	Δρmax = 0.86 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
As1	0.851830 (19)	0.703422 (18)	0.496255 (12)	0.01802 (6)
S1	0.60863 (5)	1.03859 (5)	0.17158 (3)	0.03019 (13)
S2	0.83788 (6)	1.05708 (5)	0.78874 (3)	0.02996 (13)
S3	1.44348 (5)	0.76333 (6)	0.50798 (4)	0.03192 (14)
C1	0.78015 (19)	0.80668 (17)	0.40006 (12)	0.0183 (4)
C2	0.64685 (19)	0.81069 (18)	0.35944 (13)	0.0224 (4)
H2A	0.5944	0.7653	0.3790	0.027*
C3	0.59018 (19)	0.88051 (19)	0.29053 (12)	0.0234 (4)
H3A	0.5008	0.8824	0.2651	0.028*
C4	0.66768 (19)	0.94822 (18)	0.25918 (12)	0.0204 (4)
C5	0.80152 (19)	0.94533 (17)	0.29981 (11)	0.0192 (4)
H5A	0.8542	0.9905	0.2802	0.023*
C6	0.85652 (18)	0.87601 (17)	0.36893 (11)	0.0183 (4)
H6A	0.9458	0.8754	0.3952	0.022*
C7	0.84768 (18)	0.81425 (17)	0.58127 (12)	0.0178 (4)
C8	0.8544 (2)	0.77177 (19)	0.65816 (13)	0.0262 (5)
H8A	0.8605	0.6918	0.6680	0.031*
C9	0.8520 (2)	0.8473 (2)	0.71996 (13)	0.0286 (5)
H9A	0.8567	0.8174	0.7709	0.034*
C10	0.84255 (19)	0.96751 (18)	0.70672 (12)	0.0204 (4)
C11	0.83575 (18)	1.01047 (18)	0.63009 (12)	0.0197 (4)
H11A	0.8293	1.0904	0.6201	0.024*
C12	0.83859 (18)	0.93414 (17)	0.56862 (12)	0.0186 (4)
H12A	0.8343	0.9639	0.5178	0.022*
C13	1.03380 (18)	0.72022 (17)	0.50883 (12)	0.0178 (4)
C14	1.0843 (2)	0.64556 (18)	0.46419 (12)	0.0214 (4)
H14A	1.0332	0.5857	0.4330	0.026*
C15	1.2091 (2)	0.65933 (19)	0.46564 (12)	0.0230 (4)
H15A	1.2408	0.6092	0.4351	0.028*
C16	1.28772 (19)	0.74795 (19)	0.51259 (12)	0.0209 (4)
C17	1.24043 (19)	0.81979 (18)	0.56012 (12)	0.0198 (4)
H17A	1.2931	0.8768	0.5938	0.024*
C18	1.11392 (19)	0.80605 (17)	0.55710 (11)	0.0190 (4)
H18A	1.0825	0.8555	0.5881	0.023*
C19	0.4396 (2)	1.0054 (2)	0.12929 (14)	0.0353 (6)
H19A	0.4018	1.0427	0.0765	0.053*
H19B	0.3984	1.0333	0.1660	0.053*
H19C	0.4281	0.9225	0.1228	0.053*
C20	0.7909 (3)	1.1960 (2)	0.73922 (14)	0.0367 (6)
H20A	0.7705	1.2484	0.7761	0.055*
H20B	0.7164	1.1862	0.6899	0.055*
H20C	0.8606	1.2276	0.7252	0.055*
C21	1.5139 (2)	0.8774 (3)	0.58105 (19)	0.0518 (8)
H21A	1.5994	0.8937	0.5821	0.078*
H21B	1.5180	0.8531	0.6350	0.078*
H21C	1.4619	0.9465	0.5652	0.078*

	U11	U22	U33	U12	U13	U23
As1	0.01501 (10)	0.01771 (11)	0.02239 (10)	−0.00177 (8)	0.00793 (8)	−0.00007 (8)
S1	0.0216 (3)	0.0365 (3)	0.0284 (3)	−0.0021 (2)	0.0039 (2)	0.0102 (2)
S2	0.0388 (3)	0.0320 (3)	0.0207 (2)	0.0064 (3)	0.0126 (2)	−0.0011 (2)
S3	0.0181 (3)	0.0435 (4)	0.0390 (3)	0.0006 (2)	0.0161 (2)	−0.0026 (3)
C1	0.0159 (9)	0.0198 (10)	0.0199 (9)	−0.0017 (8)	0.0074 (7)	−0.0023 (7)
C2	0.0152 (9)	0.0263 (11)	0.0274 (10)	−0.0050 (8)	0.0096 (8)	0.0010 (8)
C3	0.0136 (9)	0.0296 (12)	0.0265 (10)	−0.0020 (8)	0.0065 (8)	0.0013 (9)
C4	0.0186 (10)	0.0214 (10)	0.0210 (9)	0.0002 (8)	0.0069 (8)	−0.0015 (8)
C5	0.0176 (9)	0.0208 (10)	0.0208 (9)	−0.0029 (8)	0.0088 (7)	−0.0033 (8)
C6	0.0135 (9)	0.0216 (10)	0.0210 (9)	−0.0027 (7)	0.0075 (7)	−0.0029 (8)
C7	0.0122 (9)	0.0209 (10)	0.0220 (9)	0.0005 (7)	0.0081 (7)	0.0017 (7)
C8	0.0351 (13)	0.0199 (11)	0.0282 (11)	0.0051 (9)	0.0168 (9)	0.0061 (8)
C9	0.0379 (13)	0.0277 (12)	0.0230 (10)	0.0047 (10)	0.0143 (9)	0.0071 (9)
C10	0.0164 (9)	0.0260 (11)	0.0199 (9)	0.0016 (8)	0.0077 (7)	0.0003 (8)
C11	0.0166 (9)	0.0191 (10)	0.0243 (9)	0.0007 (8)	0.0085 (8)	0.0010 (8)
C12	0.0175 (9)	0.0197 (10)	0.0210 (9)	−0.0007 (8)	0.0097 (7)	0.0037 (7)
C13	0.0145 (9)	0.0195 (10)	0.0196 (9)	−0.0002 (7)	0.0061 (7)	0.0016 (7)
C14	0.0210 (10)	0.0200 (10)	0.0232 (9)	0.0013 (8)	0.0078 (8)	−0.0015 (8)
C15	0.0215 (10)	0.0256 (11)	0.0239 (10)	0.0044 (9)	0.0106 (8)	−0.0015 (8)
C16	0.0156 (9)	0.0248 (11)	0.0238 (10)	0.0037 (8)	0.0087 (8)	0.0046 (8)
C17	0.0137 (9)	0.0239 (11)	0.0215 (9)	0.0006 (7)	0.0059 (7)	0.0019 (8)
C18	0.0169 (9)	0.0215 (10)	0.0194 (9)	0.0011 (8)	0.0076 (7)	0.0001 (7)
C19	0.0242 (12)	0.0306 (13)	0.0392 (13)	0.0000 (10)	−0.0033 (10)	0.0034 (10)
C20	0.0505 (16)	0.0318 (14)	0.0249 (11)	0.0106 (11)	0.0100 (11)	−0.0038 (9)
C21	0.0193 (12)	0.069 (2)	0.0692 (19)	−0.0159 (13)	0.0189 (12)	−0.0260 (16)

As1—C7	1.9574 (19)	C9—H9A	0.9300
As1—C13	1.960 (2)	C10—C11	1.392 (3)
As1—C1	1.9660 (19)	C11—C12	1.387 (3)
S1—C4	1.760 (2)	C11—H11A	0.9300
S1—C19	1.793 (2)	C12—H12A	0.9300
S2—C10	1.768 (2)	C13—C18	1.388 (3)
S2—C20	1.795 (2)	C13—C14	1.397 (3)
S3—C16	1.765 (2)	C14—C15	1.384 (3)
S3—C21	1.793 (3)	C14—H14A	0.9300
C1—C2	1.393 (3)	C15—C16	1.395 (3)
C1—C6	1.401 (3)	C15—H15A	0.9300
C2—C3	1.388 (3)	C16—C17	1.392 (3)
C2—H2A	0.9300	C17—C18	1.393 (3)
C3—C4	1.402 (3)	C17—H17A	0.9300
C3—H3A	0.9300	C18—H18A	0.9300
C4—C5	1.398 (3)	C19—H19A	0.9600
C5—C6	1.384 (3)	C19—H19B	0.9600
C5—H5A	0.9300	C19—H19C	0.9600
C6—H6A	0.9300	C20—H20A	0.9600
C7—C12	1.389 (3)	C20—H20B	0.9600
C7—C8	1.395 (3)	C20—H20C	0.9600
C8—C9	1.384 (3)	C21—H21A	0.9600
C8—H8A	0.9300	C21—H21B	0.9600
C9—C10	1.394 (3)	C21—H21C	0.9600
C7—As1—C13	98.73 (8)	C11—C12—C7	121.50 (18)
C7—As1—C1	97.87 (8)	C11—C12—H12A	119.2
C13—As1—C1	97.15 (8)	C7—C12—H12A	119.2
C4—S1—C19	103.97 (10)	C18—C13—C14	118.11 (18)
C10—S2—C20	102.53 (10)	C18—C13—As1	123.30 (15)
C16—S3—C21	103.15 (11)	C14—C13—As1	118.53 (15)
C2—C1—C6	117.67 (18)	C15—C14—C13	121.01 (19)
C2—C1—As1	118.95 (14)	C15—C14—H14A	119.5
C6—C1—As1	123.38 (14)	C13—C14—H14A	119.5
C3—C2—C1	121.84 (18)	C14—C15—C16	120.41 (19)
C3—C2—H2A	119.1	C14—C15—H15A	119.8
C1—C2—H2A	119.1	C16—C15—H15A	119.8
C2—C3—C4	120.00 (19)	C17—C16—C15	119.12 (18)
C2—C3—H3A	120.0	C17—C16—S3	123.24 (16)
C4—C3—H3A	120.0	C15—C16—S3	117.64 (16)
C5—C4—C3	118.59 (18)	C16—C17—C18	119.79 (19)
C5—C4—S1	116.77 (15)	C16—C17—H17A	120.1
C3—C4—S1	124.64 (15)	C18—C17—H17A	120.1
C6—C5—C4	120.71 (18)	C13—C18—C17	121.48 (19)
C6—C5—H5A	119.6	C13—C18—H18A	119.3
C4—C5—H5A	119.6	C17—C18—H18A	119.3
C5—C6—C1	121.18 (18)	S1—C19—H19A	109.5
C5—C6—H6A	119.4	S1—C19—H19B	109.5
C1—C6—H6A	119.4	H19A—C19—H19B	109.5
C12—C7—C8	118.15 (18)	S1—C19—H19C	109.5
C12—C7—As1	122.86 (14)	H19A—C19—H19C	109.5
C8—C7—As1	118.99 (15)	H19B—C19—H19C	109.5
C9—C8—C7	120.8 (2)	S2—C20—H20A	109.5
C9—C8—H8A	119.6	S2—C20—H20B	109.5
C7—C8—H8A	119.6	H20A—C20—H20B	109.5
C8—C9—C10	120.74 (19)	S2—C20—H20C	109.5
C8—C9—H9A	119.6	H20A—C20—H20C	109.5
C10—C9—H9A	119.6	H20B—C20—H20C	109.5
C11—C10—C9	118.78 (18)	S3—C21—H21A	109.5
C11—C10—S2	123.63 (16)	S3—C21—H21B	109.5
C9—C10—S2	117.58 (15)	H21A—C21—H21B	109.5
C12—C11—C10	120.06 (19)	S3—C21—H21C	109.5
C12—C11—H11A	120.0	H21A—C21—H21C	109.5
C10—C11—H11A	120.0	H21B—C21—H21C	109.5
C7—As1—C1—C2	−89.18 (16)	C8—C9—C10—S2	179.13 (18)
C13—As1—C1—C2	170.93 (16)	C20—S2—C10—C11	11.2 (2)
C7—As1—C1—C6	91.80 (17)	C20—S2—C10—C9	−167.94 (19)
C13—As1—C1—C6	−8.09 (17)	C9—C10—C11—C12	−0.1 (3)
C6—C1—C2—C3	−0.1 (3)	S2—C10—C11—C12	−179.27 (15)
As1—C1—C2—C3	−179.13 (16)	C10—C11—C12—C7	0.2 (3)
C1—C2—C3—C4	1.0 (3)	C8—C7—C12—C11	−0.2 (3)
C2—C3—C4—C5	−1.3 (3)	As1—C7—C12—C11	179.94 (14)
C2—C3—C4—S1	179.00 (16)	C7—As1—C13—C18	−9.49 (18)
C19—S1—C4—C5	172.71 (16)	C1—As1—C13—C18	89.65 (17)
C19—S1—C4—C3	−7.6 (2)	C7—As1—C13—C14	173.47 (16)
C3—C4—C5—C6	0.8 (3)	C1—As1—C13—C14	−87.39 (16)
S1—C4—C5—C6	−179.54 (15)	C18—C13—C14—C15	−2.3 (3)
C4—C5—C6—C1	0.2 (3)	As1—C13—C14—C15	174.91 (15)
C2—C1—C6—C5	−0.5 (3)	C13—C14—C15—C16	0.6 (3)
As1—C1—C6—C5	178.50 (14)	C14—C15—C16—C17	2.2 (3)
C13—As1—C7—C12	79.74 (17)	C14—C15—C16—S3	−177.57 (16)
C1—As1—C7—C12	−18.79 (18)	C21—S3—C16—C17	4.1 (2)
C13—As1—C7—C8	−100.12 (17)	C21—S3—C16—C15	−176.15 (18)
C1—As1—C7—C8	161.35 (16)	C15—C16—C17—C18	−3.1 (3)
C12—C7—C8—C9	0.0 (3)	S3—C16—C17—C18	176.61 (15)
As1—C7—C8—C9	179.87 (17)	C14—C13—C18—C17	1.3 (3)
C7—C8—C9—C10	0.1 (3)	As1—C13—C18—C17	−175.74 (14)
C8—C9—C10—C11	−0.1 (3)	C16—C17—C18—C13	1.4 (3)

Cg1 is the centroid of the C7–C12 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21A···Cg1i	0.96	2.55	3.441 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21A⋯Cg1i	0.96	2.55	3.441 (3)	155

Symmetry code: (i) .